Organophosphorus-catalyzed diaza-Wittig reaction: application to the synthesis of pyridazines

被引：33

作者：

Abed, Hassen Bel ^{[1
]}

Mammoliti, Oscar ^{[2
]}

Bande, Omprakash ^{[1
]}

Van Lommen, Guy ^{[2
]}

Herdewijn, Piet ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Leuven, Belgium

[2] Galapagos NV, Med Chem Lab, B-2800 Mechelen, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 36期

关键词：

DIELS-ALDER REACTIONS; CONVENIENT STRATEGY; APPEL; DERIVATIVES;

D O I：

10.1039/c4ob01201a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The elaboration of the first organophosphorus-catalyzed diaza-Wittig reaction is reported. This catalytic reaction is applied to the synthesis of substituted pyridazine and phthalazine derivatives bearing electron-withdrawing groups with good to excellent yields from substrates containing a diazo functionality as the starting material and a phospholene oxide as the catalyst.

引用

页码：7159 / 7166

页数：8

共 52 条

[1] A novel and convenient strategy for the synthesis of phthalazines from an aryne precursor [J].

Abed, Hassen Bel ;

Bande, Omprakash ;

Mammoliti, Oscar ;

Van Lommen, Guy ;

Herdewijn, Piet .

TETRAHEDRON LETTERS, 2013, 54 (51) :7056-7058

[2] Strategy for the Synthesis of Pyridazine Heterocycles and Their Derivatives [J].

Abed, Hassen Bel ;

Mammoliti, Oscar ;

Bande, Omprakash ;

Van Lommen, Guy ;

Herdewijn, Piet .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :7845-7858

[3] Simple approach to the synthesis of 3-fluoro pyrazolo[1,5-a]pyrimidine analogues [J].

Abed, Hassen Bel ;

Mammoliti, Oscar ;

Van Lommen, Guy ;

Herdewijn, Piet .

TETRAHEDRON LETTERS, 2013, 54 (21) :2612-2614

[4] A short and convenient strategy for the synthesis of pyridazines via Diaza-Wittig reaction [J].

Abed, Hassen Bel ;

Mammoliti, Oscar ;

Van Lommen, Guy ;

Herdewijn, Piet .

TETRAHEDRON LETTERS, 2012, 53 (48) :6489-6491

[5] Synthesis and molecular structure of 6-aryl-3-ethoxycarbonyl-4-hydroxypyridazines [J].

Aliev, ZG ;

Vyaznikova, NG ;

Zalesov, VV ;

Kataev, SS ;

Andreichikov, YS ;

Atovmyan, LO .

RUSSIAN CHEMICAL BULLETIN, 1997, 46 (12) :2142-2145

[6] Phosphorus(V)-catalyzed deoxydichlorination reactions of aldehydes [J].

An, Jie ;

Tang, Xiaoping ;

Moore, Joshua ;

Lewis, William ;

Denton, Ross M. .

TETRAHEDRON, 2013, 69 (41) :8769-8776

[7] TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].

APPEL, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811

[8]

Appel R., 1975, Angew. Chem, V87, P863

[9] A Novel and Convenient Protocol for Synthesis of Pyridazines [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Filippone, Paolino ;

Perrulli, Francesca R. ;

Santeusanio, Stefania .

ORGANIC LETTERS, 2009, 11 (02) :309-312

[10]

Boger D.L., 1989, PROG HETEROCYCL CHEM, V1, P30

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